Hey Dan:
I'm in the habit of importing stuff frequently. Here's the rub:
Most of what you purchase south of the border must be made in the US of A. If it is made in China, I would suggest that you find the equivalent in Canada. It will be cheaper here than in the US.
Next, DO NOT SHIP United Parcel Service (UPS). I just brought in a part for a shower rod only to find that the piece was free but UPS wanted $24 in brokerage fees for something that was marked "N/C." The driver said that the shipper should have marked it "no commercial value." In my books, UPS is now getting famous for fine print.
My experience is that United States Postal Service (USPS) can ship cheaper and faster than UPS. Further, Canada Customs merely processes the item and adds GST and PST to the invoice price. It is seldom that I have to pay duties on anything made in the US.
That said, do your homework. If you order it from the US, make sure it isn't available here. I live near Quebec City so I have language, measurement and terminology problems as well as import problems. Even so, I can still get most things here. Those I can't I would suggest Preston Hardware in Ottawa, Tegs Tools in Hamilton, Weeks Home Hardware in Waterdown, Henry's Tools in St. Catherines as possible sources for importing. Be sure to do price comparison. Don't be stuck on a brand name. A Makita 3612C with a red case and King Canada Performance Plus label is still a 3612C without the electric brake.
I forgot to add a few things. Tegs can have custom bits made, either drill, router or shaper. They've been in business a long time and they know people who know people who can get things done. Tegs also has a decent web site and will ship almost anywhere mail goes. I've been in Preston Hdwe and found them too pricey but the clerk told me he'd compete. Check first. Weeks claim to fame is they handle SteelCity, the full line. The Canadian rep for SteelCity lives less than 1/2 hour from them. Henry's Tools in St. Catherines has the occasional good bargain and carry some interesting tools but they appear to be a local vendor. You might try them but don't be surprised if they turn down a small order.
I would also suggest that you ask your US supplier if they can ship from a Canadian source. For example, Southeast Tools have a distributor in Toronto. Carbide Processors also have a warehouse somewhere in Ontario. Many US vendors are now recognizing that their profitability is being dictated by Canadian sales so we're getting better service than ever before.